905534

Sigma-Aldrich

(2-(Phenoxycarbonyl)phenyl)boronic acid

greener alternative

≥95%

Empirical Formula (Hill Notation):
C13H11BO4
CAS Number:
Molecular Weight:
242.04
MDL number:

assay

≥95%

form

powder or crystals

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

150-152 °C

greener alternative category

Aligned

storage temp.

2-8°C

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

(2-(Phenoxycarbonyl)phenyl)boronic acid is a boronic acid catalyst from the Hall Group developed for chemoselective activation of oxime N−OH bonds for the preparation of functionalized amide compounds via Beckmann Rearrangement. This catalyst is efficient to transform various diaryl, aryl-alkyl, heteroaryl-alkyl, and dialkyl oximes to amide products under ambient conditions.

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Xiaobin Mo et al.
Journal of the American Chemical Society, 140(15), 5264-5271 (2018-03-23)
Catalytic activation of hydroxyl functionalities is of great interest for the production of pharmaceuticals and commodity chemicals. Here, 2-alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid were identified as efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann...
Scope and Mechanism of a True Organocatalytic Beckmann Rearrangement with a Boronic Acid/Perfluoropinacol System under Ambient Conditions.
Mo X, et al.
Journal of the American Chemical Society, 140(15), 5264-5271 (2018)

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